10,12,15-Octadecatrienoic acid, 9-(benzoyloxy)-, methyl ester, (E,Z,Z)-

Base Information

• Chemical Name: 10,12,15-Octadecatrienoic acid, 9-(benzoyloxy)-, methyl ester, (E,Z,Z)-
• CAS No.: 106031-51-0
• Molecular Formula: C26H36O4
• Molecular Weight: 412.569
• Mol file: 106031-51-0.mol

Synonyms:

Chemical Property of 10,12,15-Octadecatrienoic acid, 9-(benzoyloxy)-, methyl ester, (E,Z,Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 10,12,15-Octadecatrienoic acid, 9-(benzoyloxy)-, methyl ester, (E,Z,Z)-

There total 11 articles about 10,12,15-Octadecatrienoic acid, 9-(benzoyloxy)-, methyl ester, (E,Z,Z)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

methyl-(E)-9-benzoyloxy-11-formyl-10-undecenoate (106031-50-9) + (3Z)-3-hexenyltriphenylphosphonium bromide (21676-05-1) → methyl (10E,12Z,15Z)-9-benzoyloxy octadecatrienoate (106031-51-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 12h;

DOI:10.1016/S0040-4039(00)84508-6

Reference yield:

3-hexyn-1-ol (1002-28-4) → methyl (10E,12Z,15Z)-9-benzoyloxy octadecatrienoate (106031-51-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / H₂ / PII Nickel / ethanol / 760 Torr

2: triethylamine / CH₂Cl₂ / 2 h / Ambient temperature

3: lithium bromide / acetone / 12 h / Ambient temperature

4: 2.1 g / benzene / 36 h / Heating

5: 55 percent / potassium tert. butoxide / tetrahydrofuran / 8 h / 20 °C

With potassium tert-butylate; hydrogen; triethylamine; lithium bromide; PII Nickel; In tetrahydrofuran; ethanol; dichloromethane; acetone; benzene;

DOI:10.1016/S0040-4020(01)90314-X

Reference yield:

Methyl 10-undecenoate (111-81-9) → methyl (10E,12Z,15Z)-9-benzoyloxy octadecatrienoate (106031-51-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / selenium dioxide, tert-butyl hydroperoxide / CH₂Cl₂ / 48 h / Ambient temperature

2: 90 percent / pyridine / 6 h / Ambient temperature

3: 50 percent / O₃, dimethylsulphite / methanol / 0.33 h

4: 80 percent / benzene / 6 h / Heating

5: 55 percent / potassium tert. butoxide / tetrahydrofuran / 8 h / 20 °C

With pyridine; tert.-butylhydroperoxide; selenium(IV) oxide; dimethylsulfite; potassium tert-butylate; ozone; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)90314-X

upstream raw materials:

methyl-(E)-9-benzoyloxy-11-formyl-10-undecenoate

(3Z)-3-hexenyltriphenylphosphonium bromide

methyl 9-hydroxylinelonate

benzoyl chloride

Refernces

• 1、 Rama Rao,Reddy,Purandare,Varaprasad Ch.. "Stereoselective synthesis of unsaturated C-18 hydroxy fatty acids. The self defensive substances". . p. 4385 - 4394. Retrieved 2007/10/02.